Reaktionsgleichung
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[CH2:15][C@H:14]2[C:16]([OH:18])=O)[CH:9]=[CH:10][C:11]=1[F:12]>C1(C)C=CC=CC=1>[F:5][C:6]1[CH:7]=[C:8]([C@@H:13]2[CH2:15][C@H:14]2[C:16]([Cl:3])=[O:18])[CH:9]=[CH:10][C:11]=1[F:12]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 35 °C
Versuchsvorschrift
Thionyl chloride (72.65 g, 1.21 molar equivalents) was added to the stirred toluene solution of (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid (18 wt %, net 100.00 g, 504.62 mmol). The mixture was stirred at 35° C. for 6 hours, then concentrated under reduced pressure to give a solution of (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarbonyl chloride. To a mixture of 28% ammonia aqueous solution (122.55 g, 4.00 molar equivalents), water (300.4 g) and ethyl acetate (700.2 g), the solution of (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarbonyl chloride obtained above was gradually added with stirring below 10° C. The reaction mixture was allowed to stir below 10° C. for 1 hour. The mixture was neutralized with 35% hydrochloric acid, then the organic layer was separated and washed with water. The resultant solution was concentrated azeotropically under reduced pressure to give a slurry of (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxamide. The resultant slurry was heated to obtain a clear solution, and cooled for crystallization. Hexane was added to the slurry, then the precipitates were collected by filtration and dried to give (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxamide (net 91.12 g, Yield: 92%).
Aufarbeitung
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-a81992e723204e939a868423b7136969
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08026396B2
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